Tommy Long
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  • The Quiet Update

    May 25, 2026

    How groups update when reality moves faster than identity can - or how they don't. AI is just the case study where it's happening fast enough to watch in real time.

  • The Principal

    May 19, 2026

    Last week I wrote that the pure manager was structurally obsolete. This week ClickUp's CEO explained exactly why - and pointed at what replaces it.

  • The Workaround

    May 9, 2026

    Brian Armstrong declared the end of the pure manager. He's right. But the pure manager wasn't killed by AI - it was always a workaround.

  • The Myth of Non-Determinism

    April 18, 2026

    "But LLMs are non-deterministic" is one of the most common objections to AI in production. It's usually aimed at the wrong thing.

  • Three Months Without Code

    April 9, 2026

    The longest break from the keyboard I've taken since the 1990s. And somehow the most productive stretch of my career.

  • The New Programming Language

    March 26, 2026

    I just built my first Python app. I still don't know how to write Python.

  • Where Engineering Leverage Goes Next

    March 10, 2026

    AI is making implementation cheaper. That completely shifts where teams find leverage.

  • The Pin Factory, The Copilot and The Agent

    January 31, 2026

    Adam Smith's pin factory returns—only now we're spinning up agents instead of hiring workers.

  • Less Is More: Claude Code’s Advantage Over Cursor

    January 10, 2026

    I love Cursor but I’ve recently switched to Claude Code (CLI) and I can’t see myself moving back anytime soon.

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